Modern reflection about the good life and the good society has been dominated by a spirit of liberal optimism, according to which people typically know what’s good for them and make prudent choices in pursuit of their interests. As a result, people tend to do best, and pretty well at that, when given the greatest possible freedom to live as they wish. This appealing doctrine rests on a bold assumption about human psychology: namely, that people have a high degree of aptitude for securing their well-being given arbitrarily high levels of “option freedom.” Yet a large body of empirical research suggests that people are systematically prone to make a variety of serious errors in the pursuit of happiness. These errors are probably serious enough to place liberal optimism’s psychological assumptions in doubt. If people do tend to fare best in the option-rich environments traditionally favored by liberal moderns, notably classical economists, this may not be mainly through the prudent exercise of choice. Or perhaps human beings actually benefit from certain constraints or burdens on choice.